CA2458626C - Lipid derivatives of aminoglycosides - Google Patents
Lipid derivatives of aminoglycosides Download PDFInfo
- Publication number
- CA2458626C CA2458626C CA2458626A CA2458626A CA2458626C CA 2458626 C CA2458626 C CA 2458626C CA 2458626 A CA2458626 A CA 2458626A CA 2458626 A CA2458626 A CA 2458626A CA 2458626 C CA2458626 C CA 2458626C
- Authority
- CA
- Canada
- Prior art keywords
- chosen
- transfecting
- composition according
- cells
- nucleic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229940126575 aminoglycoside Drugs 0.000 title claims abstract description 32
- 150000002632 lipids Chemical class 0.000 title claims description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 102000039446 nucleic acids Human genes 0.000 claims abstract description 64
- 108020004707 nucleic acids Proteins 0.000 claims abstract description 64
- 150000007523 nucleic acids Chemical class 0.000 claims abstract description 64
- 238000001890 transfection Methods 0.000 claims abstract description 45
- 238000000338 in vitro Methods 0.000 claims abstract description 26
- 125000006850 spacer group Chemical group 0.000 claims abstract description 12
- 108090000623 proteins and genes Proteins 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 74
- 108020004414 DNA Proteins 0.000 claims description 62
- MWRBNPKJOOWZPW-CLFAGFIQSA-N dioleoyl phosphatidylethanolamine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCC MWRBNPKJOOWZPW-CLFAGFIQSA-N 0.000 claims description 53
- 102000004169 proteins and genes Human genes 0.000 claims description 49
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 30
- 229920001223 polyethylene glycol Polymers 0.000 claims description 22
- 235000012000 cholesterol Nutrition 0.000 claims description 19
- -1 isepamycin Chemical compound 0.000 claims description 19
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- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 claims description 17
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- 108090000765 processed proteins & peptides Proteins 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 11
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- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 claims description 5
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- UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 claims description 4
- 230000003834 intracellular effect Effects 0.000 claims description 4
- UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 claims description 4
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- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 4
- JNUKAMAZVDNYCT-ZFYYWSQPSA-N (3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-16-carboxamide Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(C(N)=O)[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 JNUKAMAZVDNYCT-ZFYYWSQPSA-N 0.000 claims description 3
- XIIAYQZJNBULGD-UHFFFAOYSA-N (5alpha)-cholestane Natural products C1CC2CCCCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 XIIAYQZJNBULGD-UHFFFAOYSA-N 0.000 claims description 3
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- XIIAYQZJNBULGD-LDHZKLTISA-N cholestane Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 XIIAYQZJNBULGD-LDHZKLTISA-N 0.000 claims description 3
- 229960003807 dibekacin Drugs 0.000 claims description 3
- JJCQSGDBDPYCEO-XVZSLQNASA-N dibekacin Chemical compound O1[C@H](CN)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N JJCQSGDBDPYCEO-XVZSLQNASA-N 0.000 claims description 3
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- 229930003231 vitamin Natural products 0.000 claims description 3
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 claims description 2
- YGPZWPHDULZYFR-DPAQBDIFSA-N (3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-amine Chemical compound C1C=C2C[C@@H](N)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 YGPZWPHDULZYFR-DPAQBDIFSA-N 0.000 claims description 2
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 2
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims description 2
- LRYZPFWEZHSTHD-HEFFAWAOSA-O 2-[[(e,2s,3r)-2-formamido-3-hydroxyoctadec-4-enoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical class CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](NC=O)COP(O)(=O)OCC[N+](C)(C)C LRYZPFWEZHSTHD-HEFFAWAOSA-O 0.000 claims description 2
- ZXWQZGROTQMXME-WXUJBLQXSA-N 2-hydroxy-n-[(e,2s,3r)-3-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]tetracosanamide Chemical class CCCCCCCCCCCCCCCCCCCCCCC(O)C(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O ZXWQZGROTQMXME-WXUJBLQXSA-N 0.000 claims description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR01/11199 | 2001-08-29 | ||
| FR0111199A FR2829136B1 (fr) | 2001-08-29 | 2001-08-29 | Derives lipidiques d'aminoglycosides |
| US33145201P | 2001-11-16 | 2001-11-16 | |
| US60/331,452 | 2001-11-16 | ||
| PCT/FR2002/002959 WO2003018603A1 (fr) | 2001-08-29 | 2002-08-29 | Derives lipidiques d'aminoglycosides_pour la transfection |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2458626A1 CA2458626A1 (en) | 2003-03-06 |
| CA2458626C true CA2458626C (en) | 2011-05-03 |
Family
ID=26213158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2458626A Expired - Lifetime CA2458626C (en) | 2001-08-29 | 2002-08-29 | Lipid derivatives of aminoglycosides |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1430074B1 (de) |
| JP (1) | JP4629333B2 (de) |
| AT (1) | ATE430758T1 (de) |
| AU (1) | AU2002334051B2 (de) |
| CA (1) | CA2458626C (de) |
| DE (1) | DE60232258D1 (de) |
| WO (1) | WO2003018603A1 (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2665403C (en) * | 2006-10-04 | 2015-06-23 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Compositions comprising a sirna and lipidic 4,5-disubstituted 2-deoxystreptamine ring aminoglycoside derivatives and uses thereof |
| WO2010026537A1 (en) | 2008-09-05 | 2010-03-11 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Novel multimodular assembly useful for intracellular delivery |
| EP3125945B1 (de) | 2014-04-01 | 2019-09-11 | Institut National de la Sante et de la Recherche Medicale (INSERM) | Verkappte und kappenlose rna-moleküle und blockcopolymere zur intrazellularen bereitstellung von rna |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996024334A1 (en) * | 1995-02-10 | 1996-08-15 | Nexstar Pharmaceuticals, Inc. | Lipid constructs for cytoplasmic delivery of agents |
| FR2741066B1 (fr) * | 1995-11-14 | 1997-12-12 | Rhone Poulenc Rorer Sa | Nouveaux agents de transfection et leurs applications pharmaceutiques |
| FR2764304B1 (fr) * | 1997-06-06 | 1999-07-16 | Rhone Poulenc Rorer Sa | Nouvelle classe d'agents transfectants cationiques des acides nucleiques |
| CA2305575A1 (en) * | 1997-09-08 | 1999-03-18 | Valentis, Inc. | Hydrophobic glycosylamine derivatives, compositions, and methods for use |
| WO2000040692A2 (en) * | 1999-01-05 | 2000-07-13 | Valentis, Inc. | Methods and compositions for delivering nucleic acids |
| GB9930533D0 (en) * | 1999-12-23 | 2000-02-16 | Mitsubishi Tokyo Pharm Inc | Nucleic acid delivery |
-
2002
- 2002-08-29 EP EP02796324A patent/EP1430074B1/de not_active Expired - Lifetime
- 2002-08-29 DE DE60232258T patent/DE60232258D1/de not_active Expired - Lifetime
- 2002-08-29 AU AU2002334051A patent/AU2002334051B2/en not_active Expired
- 2002-08-29 CA CA2458626A patent/CA2458626C/en not_active Expired - Lifetime
- 2002-08-29 WO PCT/FR2002/002959 patent/WO2003018603A1/fr not_active Ceased
- 2002-08-29 AT AT02796324T patent/ATE430758T1/de not_active IP Right Cessation
- 2002-08-29 JP JP2003523262A patent/JP4629333B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2458626A1 (en) | 2003-03-06 |
| EP1430074B1 (de) | 2009-05-06 |
| JP2005504061A (ja) | 2005-02-10 |
| AU2002334051B2 (en) | 2008-05-15 |
| WO2003018603A1 (fr) | 2003-03-06 |
| ATE430758T1 (de) | 2009-05-15 |
| JP4629333B2 (ja) | 2011-02-09 |
| DE60232258D1 (de) | 2009-06-18 |
| EP1430074A1 (de) | 2004-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20220829 |